US4332944A - Compositions and use - Google Patents
Compositions and use Download PDFInfo
- Publication number
- US4332944A US4332944A US06/281,808 US28180881A US4332944A US 4332944 A US4332944 A US 4332944A US 28180881 A US28180881 A US 28180881A US 4332944 A US4332944 A US 4332944A
- Authority
- US
- United States
- Prior art keywords
- chloro
- hydrogen
- compound according
- bromo
- methylpyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Definitions
- This invention relates to N-substituted phenyl tetrahydrophthalimides, intermediates therefor and synthesis thereof, which compounds are useful herbicides.
- N-substituted phenyl tetrahydrophthalimides of the present invention are represented by the following formula (A): ##STR1## wherein,
- n is one, two or three;
- R is hydrogen, bromo, chloro, fluoro or iodo
- W is oxygen or sulfur
- each of X and Y is, independently, selected from hydrogen, bromo, chloro, fluoro, iodo, lower alkyl, lower alkoxy, lower thioalkyl, lower haloalkoxy, nitro, lower alkoxycarbonyl and cyano.
- n R, W, X and Y is as defined above, unless otherwise specified.
- the compounds of formula A are prepared by the reaction of 3,4,5,6-tetrahydrophthalic anhydride with a substituted aniline of formula (I). ##STR2##
- the reaction is conducted at a temperature above room temperature such as the reflux temperature of the reaction mixture and is generally complete within a few hours or less.
- the substituted aniline compounds of formula (I) wherein W is oxygen can be prepared by the reaction of nitrophenol with a substituted pyridylalkyl halide to obtain the corresponding substituted nitrobenzene which is reduced to the desired substituted aniline of formula (I).
- a substituted pyridylalkyl halide for example, the reaction of 4-nitrophenol and 6-chloro-3-pyridylmethyl bromide gives 4-(2-chloro-5-pyridylmethyloxy)nitrobenzene which is then reduced to 4-(2-chloro-5-pyridylmethyloxy)aniline of formula I.
- the compounds of formula I can be prepared by the reaction of a halo-nitrobenzene with a substituted pyridylalkyl alcohol or substituted pyridylalkyl thiol followed by reduction of the nitro group.
- a halo-nitrobenzene with a substituted pyridylalkyl alcohol or substituted pyridylalkyl thiol followed by reduction of the nitro group.
- the reaction of 4-fluoronitrobenzene and 5-bromo-2-pyridine methanol gives 4-(5-bromo-2-pyridylmethyloxy)nitrobenzene which is then reduced using, for example, iron powder to give 4-(5-bromo-2-pyridylmethyloxy)aniline.
- the compounds of formula A may also be prepared by the reaction of a pyridylalkyl halide with a 3,4,5,6-tetrahydrophthalimidophenol of formula (II).
- the alcohol of formula II may be prepared by reacting together aminophenol and 3,4,5,6-tetrahydrophthalic anhydride.
- lower alkyl refers to an alkyl group of one to six carbon atoms.
- lower alkoxy refers to an alkoxy group of one to six carbon atoms.
- lower alkoxycarbonyl refers to an alkoxycarbonyl group of two to six carbon atoms.
- lower thioalkyl refers to a thioalkyl group of one to six carbon atoms such as methylthio.
- lower haloalkyl refers to a haloalkyl group of one to six carbon atoms substituted with at least one halo atom such as trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, fluoromethyl or chloromethyl.
- lower haloalkoxy refers to a haloalkoxy group of one to six carbon atoms substituted with at least one halo atom such as difluoromethoxy, dichloromethoxy, trifluoromethoxy, trichloromethoxy, fluoromethoxy or chloromethoxy.
- the compounds of formula (A) are useful for the control of weeds using pre- and/or post-emergent treatments.
- the compounds can be applied in the form of dusts, granules, solutions, emulsions, wettable powders and suspensions.
- Application of a compound of the present invention is made according to conventional procedure using from about one-forth to ten pounds per acre.
- Methods of preparing herbicidal formulations which can be used with a compound of the present invention are described in the literature along with suitable liquid and solid carriers such as in U.S. Pat. Nos. 4,192,669, 4,163,661 and 4,072,499 which are incorporated herein by reference.
- the compounds of the present invention have activity on broadleaf plants and grassy plants. The optimum usage of a compound of the present invention is readily determinable by one of ordinary skill in the art using routine testing such as greenhouse testing and small plot testing.
- each of W' and W" is oxygen or sulfur and each of R, n, W, X and Y is as defined hereinabove.
- 6-Chloronicotinic acid (3.0 g, 18.98 mmol) is dissolved in 30 ml of tetrahydrofuran (THF), with the temperature of the solution maintained below 30°.
- a 1 M solution of borane/TMF (19 ml, 19.0 mmol) is added at a rate to maintain a slow evolution of gas. This mixture is stirred at RT overnight.
- the reaction is poured onto approximately 50 g ice with 2 ml concentrated hydrochloric acid and is stirred for 1 hour. The pH of the reaction is adjusted to 5.
- the reaction is then extracted with chloroform, washed with water, dried and stripped to give 6-chloro-3-pyridinemethanol.
- 2-chloro-5-(4-nitrophenoxy)methylpyridine may be prepared by heating to 80° for 24 hours a mixture of 2-chloro-(5-chloromethyl)pyridine hydrochloride (2.0 g, 10.2 mmol), 4-nitrophenol (1.5 g, 10.2 mmol), potassium carbonate (2.8 g, 20.4 mmol) and potassium iodide (50 mg) in 40 ml of a 1:1 mixture of isopropanol and dimethylformamide. The resulting reaction mixture is poured into water, extracted with ether, washed with water, dried and stripped to give 2-chloro-5-(4-nitrophenoxy)methylpyridine.
- 2-chloro-5-(4-nitrophenoxy)ethylpyridine is prepared from the reaction of 2-chloro-5-pyridylacetic acid with borane/THF and 1-fluoro-4-nitrobenzene or, alternatively, from the reaction of 2-chloro-(5-chloroethyl)pyridine with 4 nitrophenol.
- each of the substituted methylpyridines in column I is prepared from the corresponding substituted nicotinic acid and is then reacted with 3,4,5,6-tetrahydrophthalic anhydride to yield the compound of formula (A) in column II.
- each of 2-(4-aminophenoxy)methylpyridine and 5-trifluoromethyl-2-(4-aminophenoxy)methylpyridine is reacted with 3,4,5,6-tetrahydrophthalic anhydride to yield N-4-(2-pyridylmethoxy)phenyl-3,4,5,6-tetrahydrophthalimide and N-4-[2-(5-trifluoromethylpyridyl)methoxy]phenyl-3,4,5,6-tetrahydrophthalimide, respectively.
- each of 5-chloro-2-(4-aminophenoxy)methylpyridine, 2-(4-aminophenoxy)methylpyridine and 5-trifluoromethyl-2-(4-aminophenoxy)methylpyridine may be prepared from the reaction of 4-nitrophenol with, respectively, 5-chloro-(2-chloromethyl)pyridine, (2-chloromethyl)pyridine and 5-trifluoromethyl-(2-chloromethyl)-pyridine followed by reduction with iron and ammonium chloride, following the procedure of Example 1.
- each of 2-chloro-5-(4-aminophenylthio)methylpyridine and 5-chloro-2-(4-aminophenylthio)methylpyridine is prepared from the reaction of 4-nitrobenzenethiol with, respectively, 2-chloro-5-bromomethylpyridine and 5-chloro-2-bromomethylpyridine, followed by reduction.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims (20)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/281,808 US4332944A (en) | 1981-07-09 | 1981-07-09 | Compositions and use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/281,808 US4332944A (en) | 1981-07-09 | 1981-07-09 | Compositions and use |
Publications (1)
Publication Number | Publication Date |
---|---|
US4332944A true US4332944A (en) | 1982-06-01 |
Family
ID=23078873
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/281,808 Expired - Fee Related US4332944A (en) | 1981-07-09 | 1981-07-09 | Compositions and use |
Country Status (1)
Country | Link |
---|---|
US (1) | US4332944A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4536209A (en) * | 1980-10-07 | 1985-08-20 | Mitsubishi Chemical Industries Ltd. | N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition |
US4816065A (en) * | 1986-12-23 | 1989-03-28 | Fmc Corporation | Herbicides |
WO1999038861A1 (en) * | 1998-01-29 | 1999-08-05 | Bayer Aktiengesellschaft | Substituted heteroarylmethyl compounds used as herbicides |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4225497A (en) * | 1978-02-19 | 1980-09-30 | Rhone-Poulenc Industries | Preparation of N-substituted oligo-imides |
-
1981
- 1981-07-09 US US06/281,808 patent/US4332944A/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4225497A (en) * | 1978-02-19 | 1980-09-30 | Rhone-Poulenc Industries | Preparation of N-substituted oligo-imides |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4536209A (en) * | 1980-10-07 | 1985-08-20 | Mitsubishi Chemical Industries Ltd. | N-(3-substituted oxyphenyl)tetrahydrophthalimides and herbicidal composition |
US4816065A (en) * | 1986-12-23 | 1989-03-28 | Fmc Corporation | Herbicides |
WO1999038861A1 (en) * | 1998-01-29 | 1999-08-05 | Bayer Aktiengesellschaft | Substituted heteroarylmethyl compounds used as herbicides |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3044402B2 (en) | Herbicidal carboxamide derivatives | |
JP3157234B2 (en) | Herbicidal carboxamide derivatives | |
US4130413A (en) | Heterocyclic phenyl ethers and herbicides containing same | |
AU2009313134B2 (en) | Novel halogen-substituted compounds | |
US4063928A (en) | Composition and method of controlling undesired plant growth with substituted pyridinyloxy(thio)phenyl -acetamides, -ureas and urea derivatives | |
JP4388724B2 (en) | 4-Aminopicolinates and their use as herbicides | |
US4213774A (en) | Pyridyloxy-phenoxy-α-propionic acid aminoalkyl esters | |
AU605327B2 (en) | Herbicidal fluorophenoxyphenoxyalkanoic acids and derivatives thereof | |
JPH02164866A (en) | Oxime ether derivative, production thereof and | |
WO2010133312A1 (en) | Halogen-substituted compounds as pesticides | |
JPS62142157A (en) | Manufacture of pyridyl(oxy/thio)phenoxy compound | |
US4775762A (en) | Novel (1H-1,2,3-triazol-1-yl)pyridines | |
US4332944A (en) | Compositions and use | |
EP0330939A2 (en) | Acrylic acid morpholides, their production and use | |
JP3142392B2 (en) | Herbicidal picolinamide derivatives | |
US4584396A (en) | Substituted phenoxypropionates and herbicidal compositions | |
JPH0454164A (en) | Acrylonitrile derivative having herbicidal activity | |
US4406689A (en) | Certain aralkyloxy or thio-pyridyl-imidazo-pyridines and their herbicidal use | |
JPS61282365A (en) | 1-aryl-4-cyano-5-halogenopyrazoles | |
US4233060A (en) | α-Phenoxy-thiolpropionic acids | |
EP0179015A1 (en) | 7-(Aryloxy)-2-naphthoxyalkanecarboxylic acid derivatives, processes for the preparation of these compounds, as well as agents having herbicidal activity containing these compounds | |
US4722749A (en) | Pyridinesulfonamides and their use as herbicidal agents | |
US4931452A (en) | N-cyanomethyl-2-pyridinone insecticides | |
CA1198114A (en) | Anilines and their use | |
CA2276012C (en) | 6-(nonsubstituted or substituted) phenoxy picolinic acid, process for producing the same and agricultural or horticultural fungicide using the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: ZOECON CORPORATION, 975 CALIFORNIA AVE., PALO ALTO Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:ANDERSON, RICHARD J.;LEIPPE, MICHAEL M.;REEL/FRAME:003903/0610 Effective date: 19810729 |
|
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, PL 96-517 (ORIGINAL EVENT CODE: M170); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 4 |
|
AS | Assignment |
Owner name: SANDOZ Free format text: ASSIGNS AS OF SEPT. 4, 1986 THE ENTIRE INTEREST;ASSIGNOR:ZOECON CORPORATION, 975 CALIFORNIA AVE., PALO ALTO, CA. 94304, A CORP. OF DE.;REEL/FRAME:004676/0329 Effective date: 19860904 |
|
FEPP | Fee payment procedure |
Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FEPP | Fee payment procedure |
Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
LAPS | Lapse for failure to pay maintenance fees | ||
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 19900603 |